PMID- 26612607
OWN - NLM
STAT- MEDLINE
DCOM- 20161007
LR  - 20190115
IS  - 1521-3773 (Electronic)
IS  - 1433-7851 (Print)
IS  - 1433-7851 (Linking)
VI  - 55
IP  - 2
DP  - 2016 Jan 11
TI  - Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled 
      Electron Transfer.
PG  - 539-44
LID - 10.1002/anie.201508060 [doi]
AB  - Quinones are important organic oxidants in a variety of synthetic and biological 
      contexts, and they are susceptible to activation towards electron transfer 
      through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has 
      been observed for Lewis basic, weakly oxidizing quinones, comparable activation 
      is not readily achieved when more reactive and synthetically useful 
      electron-deficient quinones are used. We have successfully employed HBD-coupled 
      electron transfer as a strategy to activate electron-deficient quinones. A 
      systematic investigation of HBDs has led to the discovery that certain dicationic 
      HBDs have an exceptionally large effect on the rate and thermodynamics of 
      electron transfer. We further demonstrate that these HBDs can be used as 
      catalysts in a quinone-mediated model synthetic transformation.
CI  - (c) 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Turek, Amanda K
AU  - Turek AK
AD  - Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 
      02138 (USA).
FAU - Hardee, David J
AU  - Hardee DJ
AD  - Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 
      02138 (USA).
FAU - Ullman, Andrew M
AU  - Ullman AM
AD  - Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 
      02138 (USA).
FAU - Nocera, Daniel G
AU  - Nocera DG
AD  - Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 
      02138 (USA). dnocera@fas.harvard.edu.
FAU - Jacobsen, Eric N
AU  - Jacobsen EN
AD  - Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 
      02138 (USA). jacobsen@chemistry.harvard.edu.
LA  - eng
GR  - R01 GM043214/GM/NIGMS NIH HHS/United States
GR  - R37 GM043214/GM/NIGMS NIH HHS/United States
GR  - GM043214/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, U.S. Gov't, Non-P.H.S.
DEP - 20151127
PL  - Germany
TA  - Angew Chem Int Ed Engl
JT  - Angewandte Chemie (International ed. in English)
JID - 0370543
RN  - 0 (Quinones)
SB  - IM
MH  - Electrons
MH  - Hydrogen Bonding
MH  - Kinetics
MH  - Quinones/*chemistry
MH  - Thermodynamics
PMC - PMC5120606
MID - NIHMS765620
OTO - NOTNLM
OT  - catalysis
OT  - electron transfer
OT  - hydrogen bonding
OT  - oxidation
OT  - quinones
EDAT- 2015/11/28 06:00
MHDA- 2016/10/08 06:00
PMCR- 2017/01/11
CRDT- 2015/11/28 06:00
PHST- 2015/08/27 00:00 [received]
PHST- 2015/10/23 00:00 [revised]
PHST- 2015/11/28 06:00 [entrez]
PHST- 2015/11/28 06:00 [pubmed]
PHST- 2016/10/08 06:00 [medline]
PHST- 2017/01/11 00:00 [pmc-release]
AID - 10.1002/anie.201508060 [doi]
PST - ppublish
SO  - Angew Chem Int Ed Engl. 2016 Jan 11;55(2):539-44. doi: 10.1002/anie.201508060. 
      Epub 2015 Nov 27.